US6221294B1 - Process for the production of cyanuric chloride moldings - Google Patents

Process for the production of cyanuric chloride moldings Download PDF

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Publication number
US6221294B1
US6221294B1 US09/593,946 US59394600A US6221294B1 US 6221294 B1 US6221294 B1 US 6221294B1 US 59394600 A US59394600 A US 59394600A US 6221294 B1 US6221294 B1 US 6221294B1
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United States
Prior art keywords
cyanuric chloride
cooling
moldings
melt
tablets
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Expired - Fee Related
Application number
US09/593,946
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English (en)
Inventor
Ralf Goedecke
Klaus Hentschel
Rolf-Dieter Möller
Knut Ehrhardt
Manfred Schmidt
Michael Kissner
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Evonik Operations GmbH
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Degussa GmbH
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Priority to US09/593,946 priority Critical patent/US6221294B1/en
Assigned to DEGUSSA AKTIENGESELLSCHAFT reassignment DEGUSSA AKTIENGESELLSCHAFT ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: HENTSCHEL, KLAUS, KISSNER, MICHAEL, EHRHARDT, KNUT, GOEDECKE, RALF, SCHMIDT, MANFRED, MOLLER, ROLF-DIETER
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
    • C07D251/28—Only halogen atoms, e.g. cyanuric chloride

Definitions

  • the present invention relates to a new product form of solid cyanuric chloride, namely moldings, especially those in tablet or flake form, and a process for producing cyanuric chloride moldings, especially tablets and flakes.
  • the deposition of pulverulent cyanuric chloride by desublimation of cyanuric chloride in vapor form can be carried out in externally cooled chambers or by introducing cyanuric chloride vapor together with an inert gas and/or an inert cooling liquid vaporizing during the deposition process, into a deposition chamber—see for example DE-PS 12 66 308 and U.S. Pat. No. 4,591,493.
  • the latter is injected through a nozzle into a deposition chamber and cooled with cycled inert cooling gases or by indirect cooling in the deposition chamber until the spray droplets deposit in crystalline form—see for example DE 28 43 379.
  • a common feature of these processes is a considerable technical expenditure on deposition chambers and devices for recycling and purifying the process gases and waste gases.
  • cyanuric chloride is always obtained in finely particulate form, in general having a maximum grain diameter of substantially less than 250 ⁇ m.
  • Such finely particulate products are of course advantageous as regards their high reactivity, but have a number of disadvantages that make a different product form desirable for many purposes.
  • a further disadvantage of finely particulate cyanuric chloride is the unsatisfactory flowability. Although the latter can admittedly be improved by adding flow auxiliaries, for example silicic acids, nevertheless the flow auxiliary reduces the product purity of the cyanuric chloride and possibly also of products prepared therefrom.
  • the flowability of solid cyanuric chloride prepared by desublimation or spray crystallization can also be improved without adding a flow auxiliary by a shear treatment of the cyanuric chloride in a kneader or mixer, especially at 60 to 120° C.; the finely pulverulent nature of the cyanuric chloride is not however affected by this process, for the mean grain size of typical embodiments is in the range from about 10 to 40 ⁇ m.
  • cyanuric chloride is also commercially available in liquid form.
  • the preparation of cyanuric chloride in liquid form is known for example from DE-PS 23 32 636.
  • the liquid cyanuric chloride product form requires however storage and transporting vessels and containers that can be heated above the melting point of cyanuric chloride. Although such equipment is economical for users having a large and regular demand for cyanuric chloride, this is not the case however for users having a small and/or irregular demand for cyanuric chloride.
  • the object of the present invention is accordingly to provide a new solid product form for cyanuric chloride that exhibits the disadvantages of finely particulate cyanuric chloride at least to a considerably lesser extent.
  • the new product form should be easier to handle in order to reduce operational malfunctions and/or health and work safety problems.
  • cyanuric chloride moldings especially tablets and flakes.
  • Such moldings conveniently have a thickness in the range from 0.5 to 3 mm, though thicker or thinner moldings are not excluded. Flakes are preferably between about 0.5 and 2 mm thick and tablets between 1 and 3 mm thick. The diameter of ellipsoidal tablets is preferably in the range from 2 to 10 mm, especially 3 to 6 mm. Flakes include flat moldings having the aforementioned thickness, roughly strip-shaped flakes having a width of between 5 and 10 mm and a length of between 10 and 50 mm, or irregularly broken flakes of similar size. Preferred moldings are substantially free of pulverulent cyanuric chloride.
  • substantially free is understood to mean that a small amount of dust, preferably less than 5 wt. %, especially less than 2 wt. %, formed by abrasion of the moldings and/or by cyanuric chloride that has sublimated on the surface of the moldings, is not excluded.
  • the product form according to the invention can be bagged and removed from drums and containers without any problem, in other words substantially without dust formation.
  • the conveyance within a production plant there are no longer any deposits and blockages of pipelines that can be eliminated only with a great deal of effort.
  • On account of the smaller surface compared to finely particulate cyanuric chloride the danger of caking and hydrolysis is substantially reduced.
  • the moldings according to the invention are also characterized by a higher purity compared to pulverulent cyanuric chloride since the hydrolyzate content is lower and flow auxiliaries are unnecessary.
  • a process for producing cyanuric chloride moldings according to the invention comprises the droplet or strip-like application of cyanuric chloride in molten form on to a surface, dissipation of the latent heat of melting of the cyanuric chloride by cooling the surface and/or contacting the melt applied to the surface with a cooling gas, and removing the solidified moldings from the surface.
  • the surface on which the cyanuric chloride melt is applied may be formed in any suitable way. It may comprise a smooth or structured surface, preferably a smooth surface cooled from the rear side. The surface may also be flat or in the form of a corrugated surface. In the case of a stationary arrangement of a flat cooled surface, additional equipment is required in order to remove the moldings from the surface, for example blade-like removal devices. Equipment known per se is used to cool the rear side of the surface, especially spraying the rear side of the surface with a liquid or gaseous medium or causing such a medium to flow thereover.
  • a cooling gas inert with respect to cyanuric chloride, for example cooled air or nitrogen, with which the melt applied to the surface is contacted.
  • a cooling gas may for example be fed directly on to the surface, or the surface is transported through a cooled chamber; the surface may for example be a conveyor belt.
  • a continuous cooling belt normally made of a metallic material that is resistant to the corrosive effects of cyanuric chloride, is used as the cooled surface.
  • the cooling belt may be cooled by spraying or causing a cooling medium to flow over the rear side.
  • Preferred cooling media are water and glycols or cooling gases.
  • An indirect cooling for example by passing the cooling belt over a cooled surface, for example internally cooled rollers or sliding table, is also possible.
  • Equipment with a cooling belt is known and is commercially available. The process can be continuously operated with such equipment.
  • the cyanuric chloride melt is applied preferably at a temperature in the range from 150 to 190° C. using suitable application devices in droplet or strip-like form or in the form of a broad band on to the surface, for example a cooling roller or cooling belt or a belt conveyed through a cooling chamber, where the droplets solidify in the form of tablets and the strips solidify as flat moldings. Continuous strips can easily be broken up, flakes of irregular shape thereby being obtained.
  • the diameter of the outlet openings of the application equipment for the melt determines the size of the droplets or the width of the jet and thus the size of the tablets or the width of the strips.
  • outlet bores having a diameter of between 1 and 3 mm or outlet slits having a similar width and a width corresponding roughly to that of the desired strip width are preferably used.
  • the surface tension of cyanuric chloride permits the formation of a stable droplet.
  • the droplets flatten out until they have completely solidified, resulting in ellipsoidal tablets.
  • Application devices operated by hydrostatic pressure for example nozzles having a diameter of between about 1 and 3 mm, are suitable for applying droplets.
  • a selective metering of the cyanuric chloride melt is also possible using metering pumps and nozzles having a diameter of between 0.5 and 2 mm. With larger nozzle diameters the area-specific heat that has to be dissipated is also larger on account of the larger droplet size.
  • the FIGURE illustrates, diagrammatically, a device for producing tablets and strip-like flakes.
  • the cyanuric chloride melt ( 4 ) is contained in the vessel ( 1 ) provided with a heating jacket ( 2 ) and temperature measuring device ( 3 ).
  • the melt passes from the vessel through a metering valve ( 5 ) provided with a heating jacket ( 6 ) to the nozzle ( 7 ).
  • a heat-transfer medium is fed through line ( 8 ); the heat-transfer medium passes from the heatable metering valve through the line ( 9 ) to the heatable vessel, from where it is removed through line ( 10 ).
  • the cooling belt device in transverse section relative to the transporting direction of the belt, includes the cooling belt ( 11 ), a housing ( 12 ) for receiving the cooling medium, as well as a feed line ( 13 ) and discharge line ( 14 ) for this medium.
  • Suitable sealing elements ( 16 ) are arranged between the housing and cooling belt in order to prevent any contact between cyanuric chloride vapor and vapors of the cooling medium, for example water vapor.
  • the drive device for the cooling belt and its return are not shown in FIG. 1 .
  • the droplets ( 17 ) leaving the nozzle fall on to the cooling belt, where they solidify.
  • the length and speed of the cooling belt are such as to permit a complete solidification of the applied melt.
  • the cooling medium is sprayed on the rear side of the cooling belt.
  • the application surface for the melt is arranged in an enclosed space connected to a waste gas treatment unit, the surface of the enclosed space opposite the application surface being heated to a temperature above the desublimation temperature of cyanuric chloride and/or in which an inert gas stream, for example nitrogen, is passed over the application surface in order to entrain sublimate with the gas.
  • an inert gas stream for example nitrogen
  • the process is simple to carry out.
  • the equipment required to carry out the process requires less investment than is needed for conventional deposition chambers plus the requisite additional equipment for spraying a cyanuric chloride melt or for the desublimation of cyanuric chloride vapor.
  • the reduced yield hitherto caused by dust and operational malfunctions in the previously known processes for producing finely particulate cyanuric chloride does not arise in the process according to the invention.
  • the cyanuric chloride moldings obtainable according to the invention are characterized by the absence of hitherto unavoidable health and work safety problems and by the fact that the tendency to agglomeration and the danger of contamination by hydrolyzate formation is reduced.
  • the cyanuric chloride moldings according to the invention can be used in the same way as finely particulate cyanuric chloride to produce secondary products from cyanuric chloride.
  • the preparation of the secondary products can be carried out in organic or aqueous phase or in two-phase solvent systems. With conversions in the suspended state it may be convenient to comminute the moldings within the reaction medium, for example by means of a wet-grinding mill.
  • Cyanuric chloride tablets and strip-shaped flakes were produced in the plant shown in the diagram.
  • the cooling belt used was cooled with water (15° C.).
  • the belt speed was 3 m/min.
  • the temperature of the cyanuric chloride melt was 182° to 183° C.
  • Tablets are obtained having an only slightly varying diameter of about 4 mm ( ⁇ 0.2 mm) and a height of about 1.5 mm.
  • the following Table shows some substance data on the tablets according to the invention compared to a conventional finely particulate cyanuric chloride (Quality F from Degussa AG).
  • the determination of the hydrolyzate content is based on the fact that hydrolysis products of cyanuric chloride are not soluble in toluene and, after dissolving the cyanuric chloride in toluene, can easily be separated and gravimetrically determined.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Processing And Handling Of Plastics And Other Materials For Molding In General (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Inorganic Fibers (AREA)
  • Catalysts (AREA)
  • Vaporization, Distillation, Condensation, Sublimation, And Cold Traps (AREA)
  • Medical Preparation Storing Or Oral Administration Devices (AREA)
  • Glanulating (AREA)
US09/593,946 1996-10-15 2000-06-15 Process for the production of cyanuric chloride moldings Expired - Fee Related US6221294B1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
US09/593,946 US6221294B1 (en) 1996-10-15 2000-06-15 Process for the production of cyanuric chloride moldings

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
DE19642449A DE19642449A1 (de) 1996-10-15 1996-10-15 Cyanurchlorid-Formlinge und Verfahren zu ihrer Herstellung
DE19642449 1996-10-15
US95079497A 1997-10-15 1997-10-15
US09/593,946 US6221294B1 (en) 1996-10-15 2000-06-15 Process for the production of cyanuric chloride moldings

Related Parent Applications (1)

Application Number Title Priority Date Filing Date
US95079497A Division 1996-10-15 1997-10-15

Publications (1)

Publication Number Publication Date
US6221294B1 true US6221294B1 (en) 2001-04-24

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US09/593,946 Expired - Fee Related US6221294B1 (en) 1996-10-15 2000-06-15 Process for the production of cyanuric chloride moldings

Country Status (9)

Country Link
US (1) US6221294B1 (fr)
EP (1) EP0837059A1 (fr)
JP (1) JPH10120661A (fr)
KR (1) KR19980032763A (fr)
AR (1) AR009381A1 (fr)
BR (1) BR9705042A (fr)
DE (1) DE19642449A1 (fr)
HR (1) HRP970548A2 (fr)
ZA (1) ZA979201B (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6372169B1 (en) * 1998-09-14 2002-04-16 Eitoku Yasuda Process for producing a plastic sheet

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19816026C1 (de) * 1998-04-09 1999-07-29 Degussa Verfahren zur Herstellung von Cyanurchlorid-Formlingen

Citations (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1266308B (de) 1965-08-21 1968-04-18 Degussa Verfahren und Vorrichtung zur Abscheidung von feinteiligem Cyanurchlorid aus der Dampfphase
US3427314A (en) 1966-09-19 1969-02-11 Monsanto Co Methods of producing trichlorocyanuric acid
US3709648A (en) * 1970-11-27 1973-01-09 Bertrams Ag Hch Apparatus for the production of blocks from sodium hydroxide solution
DE2332636A1 (de) 1973-06-27 1975-01-16 Degussa Verfahren zur herstellung von cyanurchlorid ii
US3941784A (en) 1974-12-26 1976-03-02 Monsanto Company Production of chlorocyanuric acid
DE2843379A1 (de) 1978-10-05 1980-04-10 Degussa Verfahren zum gewinnen von festem cyanurchlorid (a)
US4244722A (en) * 1977-12-09 1981-01-13 Noboru Tsuya Method for manufacturing thin and flexible ribbon of dielectric material having high dielectric constant
US4271298A (en) 1978-11-20 1981-06-02 Deutsche Gold- Und Silber-Scheideanstalt Vormals Roessler Process for the production of suspensions or solutions of cyanuric chloride in water
US4363769A (en) * 1977-11-23 1982-12-14 Noboru Tsuya Method for manufacturing thin and flexible ribbon wafer of _semiconductor material and ribbon wafer
US4389357A (en) * 1981-06-26 1983-06-21 Ashland Oil, Inc. Method for preparing thermosetting resins
US4535160A (en) 1983-10-11 1985-08-13 Skw Trostberg Aktiengesellschaft Process for obtaining solid cyanuric chloride in finely divided form
US4591493A (en) 1984-04-13 1986-05-27 Skw Trostberg Aktiengesellschaft Process for obtaining solid cyanuric chloride
CA2024800A1 (fr) 1989-09-07 1991-03-08 Alexander Skaria Methode pour ameliorer la fluidite du chlorure de cyanuryle solide
GB2239872A (en) 1990-01-10 1991-07-17 Ciba Geigy Ag Dyestuff pastilles

Patent Citations (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1266308B (de) 1965-08-21 1968-04-18 Degussa Verfahren und Vorrichtung zur Abscheidung von feinteiligem Cyanurchlorid aus der Dampfphase
US3427314A (en) 1966-09-19 1969-02-11 Monsanto Co Methods of producing trichlorocyanuric acid
US3709648A (en) * 1970-11-27 1973-01-09 Bertrams Ag Hch Apparatus for the production of blocks from sodium hydroxide solution
DE2332636A1 (de) 1973-06-27 1975-01-16 Degussa Verfahren zur herstellung von cyanurchlorid ii
US3925377A (en) 1973-06-27 1975-12-09 Degussa Process for production of cyanuric chloride
US3941784A (en) 1974-12-26 1976-03-02 Monsanto Company Production of chlorocyanuric acid
US4363769A (en) * 1977-11-23 1982-12-14 Noboru Tsuya Method for manufacturing thin and flexible ribbon wafer of _semiconductor material and ribbon wafer
US4244722A (en) * 1977-12-09 1981-01-13 Noboru Tsuya Method for manufacturing thin and flexible ribbon of dielectric material having high dielectric constant
US4250308A (en) 1978-10-05 1981-02-10 Deutsche Gold- Und Silber-Scheideanstalt Vormals Roessler Process for the recovery of solid cyanuric chloride (A)
DE2843379A1 (de) 1978-10-05 1980-04-10 Degussa Verfahren zum gewinnen von festem cyanurchlorid (a)
US4271298A (en) 1978-11-20 1981-06-02 Deutsche Gold- Und Silber-Scheideanstalt Vormals Roessler Process for the production of suspensions or solutions of cyanuric chloride in water
US4389357A (en) * 1981-06-26 1983-06-21 Ashland Oil, Inc. Method for preparing thermosetting resins
US4535160A (en) 1983-10-11 1985-08-13 Skw Trostberg Aktiengesellschaft Process for obtaining solid cyanuric chloride in finely divided form
US4591493A (en) 1984-04-13 1986-05-27 Skw Trostberg Aktiengesellschaft Process for obtaining solid cyanuric chloride
CA2024800A1 (fr) 1989-09-07 1991-03-08 Alexander Skaria Methode pour ameliorer la fluidite du chlorure de cyanuryle solide
EP0416584A1 (fr) 1989-09-07 1991-03-13 Lonza Ag Procédé pour améliorer la fluidité de chlorure de cyanuryle solide
GB2239872A (en) 1990-01-10 1991-07-17 Ciba Geigy Ag Dyestuff pastilles

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
Henglein, E., Lexikon Chemische Technik, 1. Aufl. Seite 233 f, VCH, Weinheim, 1988 (Parat), pp. 233-234.
Kirk-Othmer, Size Enlargement, "Encyclopedia of Chemical Technology", 3d Ed., vol. 21, pp. 77-105,(C)1978.
Kirk-Othmer, Size Enlargement, "Encyclopedia of Chemical Technology", 3d Ed., vol. 21, pp. 77-105,©1978.

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6372169B1 (en) * 1998-09-14 2002-04-16 Eitoku Yasuda Process for producing a plastic sheet

Also Published As

Publication number Publication date
AR009381A1 (es) 2000-04-12
HRP970548A2 (en) 1998-10-31
KR19980032763A (ko) 1998-07-25
ZA979201B (en) 1998-09-10
BR9705042A (pt) 1999-07-20
EP0837059A1 (fr) 1998-04-22
JPH10120661A (ja) 1998-05-12
DE19642449A1 (de) 1998-04-16

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